STUDIES IN THE BIOCHEMISTRY OF MICRO-ORGANISMS. 114. VIRIDICATOL AND CYCLOPENOL, METABOLITES OF PENICILLIUM VIRIDICATUM WESTLING AND PENICILLIUM CYCLOPIUM WESTLING

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Abstract
The product cyclopenin, from a strain of P. cyclopium is a mixture of 2 closely related compounds. For one of these (C17H14N2O3, m.p. 183-184[degree], [[alpha]]20 5461-291[degree] the name cyclopenin is used. The second compound (C17H14N2O4, m.p. 215[degree] (decomp.), [[alpha]]20 5461 -309[degree]) is named cyclopenol. Cyclopenin and cyclopenol are also produced by culture filtrates of a strain of P. viridicatum, from the mycelium of which are obtained 2 corresponding metabolites: viridicatin, C15H11NO2 (3-hydroxy-4-phenyl-2-quinolone), a known metabolite of this species and of P. cyclopium; and viridicatol, C15H11NO3, m.p. 280[degree]. Acid hydrolysis of cyclopenol yields CO2, methylamine and viridicatol, and a little m-hydroxybenzoic-acid. Viridicatol undergoes alkaline oxidation to an amine, C13H11NO2, which is converted by diazotization and cyclization into 2-hydroxyfluorenone. The amine is probably 2-amino-3''-hydroxybenzophenone and viridicatol is 3-hydroxy-4-(3-hydroxyphenyl)-2-quinolone. The biogenetic significance of this structure is discussed.